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At only 27, Winehouse was highly influential in the music world - but was never able to conquer her demons

Amy Winehouse, the Grammy-winning British retro-soul singer whose remarkable musical achievements were often overshadowed by her tumultuous personal life, was found dead at her home in the Camden section of London on July 23rd. Though police were calling the cause of death "unexplained" while they awaited a medical examiner's report, many have speculated that Winehouse finally succumbed to addiction following years of well-documented drug and alcohol problems. The singer was 27 years old.

Even as the initial public reaction to news of Winehouse's death focused on the sense of inevitability that accompanied it, the singer's friends and fellow musicians expressed sadness and condolences online, tweeting everything from the Fleet Foxes simple "Bummer days" to Rihanna's "Dear God have mercy! I am sick about this right now! I am genuinely heartbroken about this." Lady Gaga wrote on Twitter that "Amy changed pop music forever, I remember knowing there was hope, and feeling not alone because of her. She lived jazz, she lived the blues."

Her father Mitch – a London cab driver who recently recorded and released his own jazz album – was scheduled to perform at New York's Blue Note on Monday night, but canceled the appearance and flew home to the U.K. Her mother, Janis, told Us Weekly that Winehouse "seemed out of it" when the two met up just a day before her death. The family released a statement saying, "Our family has been left bereft by the loss of Amy, a wonderful daughter, sister, niece. She leaves a gaping hole in our lives."

Her fans had spent the past few years watching her private dramas unfold while they waited for news that Winehouse was doing well enough to make another album. But even with only a few dozen recorded tracks to her name, Winehouse was already an icon: a badass little Jewish girl with a cartoonishly massive beehive and exaggerated swooshes of eyeliner who found room between all the tattoos and scars from cutting to wear her heart on her sleeve. Moreover, there was just an undeniable power in her voice -- husky and sultry and sad, like a broken heart marinating in whiskey and cigarette smoke. It was a voice that sounded like it came from another time, echoing Sarah Vaughn, Billie Holiday and Janis Joplin. Her 2006 album Back To Black, a refreshing and stylish blend of modern and classic R&B that appealed to a huge cross-section of music fans, was an instant classic, selling close to 10 million copies worldwide. At the time of its release, the album was the highest charting U.S. debut ever by a British female. That title now belongs to U.K. soul singer Adele, just one of several artists for whom Winehouse undeniably paved the way.

"Rehab" was Winehouse to a T: wise-cracking, defiant, self-deprecating and somehow hopeful. She never made apologies for her personal demons, and the success of "Rehab" even made them her calling card. Her fucked-upness was part of her appeal, and if she could accept it, perhaps we could, too?

But in recent years, she seemed to languish in her own mess, checking in and out of treatment, getting into fights that earned her assault charges, turning up in public with sores on her face or scratches up and down her arms. According to her father, Winehouse even developed early symptoms of emphysema as a result of smoking crack cocaine and countless cigarettes. Her legal troubles kept her from getting visas to travel to the U.S. for work, and the prospect of a serious return to the studio seemed increasingly less likely.

Winehouse grew up in Southgate, North London, a blue-collar kid raised on classic pop standards by Frank Sinatra and Dinah Washington. Mitch and Janis split when Amy was nine. Though she and older brother Alex mostly lived with their mom, Amy considered herself a daddy's girl – a tattoo on her left shoulder even bore the phrase. "She was always very self-willed," Mitch told me in 2007. "Not badly behaved, but … different."

She formed a Salt-n-Pepa style rap duo called Sweet 'n Sour with her best friend when she was 10, but mostly dreamt of being a roller-skating waitress or a stage actor. She attended the Sylvia Young Theater School and the BRIT School for Performing Arts & Technology and a few others, but kept getting in trouble and eventually, around 15, Winehouse dropped out. Her brother taught her to play guitar, and she started writing her own songs and performing them at local jazz clubs. A friend helped her get into a studio to record demos, and by 2002, she had signed a publishing deal with EMI, a management deal with Simon Fuller's 19 Entertainment and a label deal with Island UK.

Winehouse recorded her first album, 2003's jazz- and hip-hop-inflected Frank, with producer Salaam Remi (Nas, Fugees, Jurassic 5). The LP earned her critical raves at home, where she initially ranked with Jamie Cullum and Katie Melua as the most promising U.K. jazz neophytes. The album went platinum in England, earned her a nomination for the Mercury Music Prize and won her the Ivor Novello Award for songwriting, but was never released in the U.S.

She told me in 2007 that she thought her transition from her early jazz sound to the Sixties R&B of Back To Black tracked with her transition from being a stoner to being a boozer. "I used to smoke a lot of weed," she said. "I suppose if you have an addictive personality then you go from one poison to the other. The whole weed mentality is very hip-hop, and when I made my first record, all I was listening to was hip-hop and jazz. The weed mentality is very defensive, very much like, 'Fuck you, you don't know me.' Whereas the drinking mentality is very 'Woe is me, oh, I love you, I'm gonna lie in the road for you, I don't even care if you never even look my way, I'm always gonna love you.'"

Though she reteamed with Remi for a portion of Back To Black's tracks, the stroke of genius was pairing her with producer Mark Ronson, who had built on his reputation as a DJ to amass production credits for Lily Allen, Ol' Dirty Bastard and Christina Aguilera. Ronson recruited eight-man Brooklyn funk and soul band the Daptones to back the singer on tracks such as "You Know I'm No Good" and "Rehab," imparting an authentic retro-cool vibe perfectly suited to Winehouse's aesthetic. "Amy is bringing a rebellious rock & roll spirit back to popular music," Ronson told me in 2007. "Those groups from the Sixties like the Shangri-Las had that kind of attitude: young girls from Queens in motorcycle jackets. Amy looks fucking cool, and she's brutally honest in her songs. It's been so long since anybody in the pop world has come out and admitted their flaws, because everyone's trying so hard to project perfection. But Amy will say, like, 'Yeah, I got drunk and fell down. So what?' She's not into self-infatuation and she doesn't chase fame. She's lucky that she's that good, because she doesn't have to."

Upon learning of Winehouse's death, Ronson expressed heartbroken shock, tweeting, "'She was my musical soulmate and like a sister to me. This is one of the saddest days of my life.'"

Back in Black was released in the U.S. in March of 2007, by which time Winehouse was racking up accolades from critics and her fellow artists. Prince started covering one of Frank's songs, and hip-hop royalty from Jay-Z (who dropped a verse on a "Rehab" remix) and Ghostface Killah (who redid "You Know I'm No Good" for his album More Fish) to Snoop Dogg sang her praises.

In 2005, she began dating her future ex-husband, Blake Fielder-Civil. The pair would hang around their local Camden bar, playing pool, drinking and picking out classic girl group and Motown tunes on the jukebox. And by the time Back to Black came out in America, she was consumed by her intense and dysfunctional relationship with Fielder-Civil. Playing gigs was secondary to spending time fussing over her "baby," and she told me she was really more interested in starting her life as a wife and mother. The pair even snuck off to get married in May of 2007, on the same day Rolling Stone was with her in Miami reporting her cover story. A little more than a year later, in July 2008, Fielder-Civil was sentenced to 27 months in jail after he was found guilty of assault and attempted bribery. Devastated at being separated from her husband, Winehouse's condition worsened. She briefly went to rehab in early 2008 after U.K. tabloid The Sun published a video of her smoking crack, but subsequently told Rolling Stone's Claire Hoffman that she did drugs while at the rehab facility.

That year, though Winehouse won five Grammys, the focus began to shift from anticipating her next album to anticipating her next public meltdown. She got in trouble with the police for drug possession and assault, and was often photographed looking seriously unwell. Friends like Courtney Love periodically tried to help her, to litte avail; after her death, Love told Rolling Stone, "I'm fucking gutted. I tried with her, I tried twice."

In early 2009, Winehouse filed for divorce from Fielder-Civil, who was still incarcerated. She retreated to St. Lucia, where she reportedly kicked hard narcotics. Though she attended treatment again in June of that year, Winehouse's father said that, this time, it was for heavy drinking rather than drugs. Last fall she told Glamour magazine that she'd been off drugs for three years. "I literally woke up one day and was like, 'I don't want to do this anymore," she said.

Winehouse showed additional signs of improvement last year, recording a cover of Lesley Gore's 1963 hit "It's My Party" for a Quincy Jones tribute album and starting her own label, Lioness, to release music by her goddaughter Dionne Bromfield, a teen soul singer after her godmother's own heart. And in March, she joined Tony Bennett at Abbey Road studios to record the Thirties jazz standard "Body And Soul" for Bennett's upcoming Duets II album. "She was an extraordinary musician with a rare intuition as a vocalist and I am truly devastated that her exceptional talent and has come to such an early end," Bennett said in a statement following her death. "She was a lovely and intelligent person and when we recorded together she gave a soulful and extraordinary performance."

As she planned for a 12-date European tour this spring, however, the singer checked herself into the Priory Clinic in London for a "rehab assessment," reportedly at her father's request. She left the clinic just a week later, with her doctors saying they would allow Winehouse to complete the rest of her treatment as an outpatient so that she could go on the road. Her representative released a statement saying that Winehouse was "now looking forward to playing shows around Europe this summer and is raring to go."

The first show on that tour, a gig at Kalemegdan Park in Belgrade, Serbia on June 18th, was nothing short of a disaster. Before an audience of 20,000, a visibly inebriated Winehouse fumbled her lyrics, missed cues, and occasionally stopped singing entirely while her backing vocalists carried on. When the crowd began booing, she threw her shoe at them. On June 20th, after damning footage of the performance went viral, Winehouse's spokesperson announced that the singer was "withdrawing from all scheduled performances," canceling the 11 remaining dates and saying: "Everyone involved wishes to do everything they can to help her return to her best and she will be given as long as it takes for this to happen."

Her final public appearance came just a few days before her death, when Winehouse showed up onstage during Bromfield's gig at the London Roundhouse, dancing nearby while Bromfield sang the Shirelles' "Mama Said."

As authorities carried Winehouse's body from her Camden home on Saturday, fans were already congregating in the nearby town square to console each other. A couple hundred mourners piled notes, flowers, candles, paintings and even stray cigarettes and bottles of wine and vodka onto a makeshift shrine. Later, the devoted headed to the Hawley Arms, Winehouse's favorite watering hole, where one fan said she recently saw Winehouse hanging out behind the bar pouring pints. Whether or not Winehouse's autopsy shows that her death was drug- or alcohol-related, her premature death is nothing short of a tragic loss to the music world. And so, in a sad footnote to an already tragic story, Winehouse now joins the ranks of the so-called 27 Club — a group of iconic musicians who died at that age including Jim Morrison, Jimi Hendrix, Janis Joplin, the Rolling Stones' Brian Jones, and Kurt Cobain.

But Winehouse's own words are perhaps her most fitting epigraph: "I wish I could say 'no regrets' and no emotional debts, and as we kiss good-bye the sun sets. So we are history, the shadow covers me, the sky above a blaze that only lovers see... My tears dry on their own."